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First Total Synthesis of Phytoprostanes with Prostaglandin-Like Configuration, Evidence for Their Formation in Edible Vegetable Oils and Orienting Study of Their Biological Activity
Chemistry - A European Journal 2021: Early View
Phytoprostanes (PhytoP) are natural products, which form in plants under oxidative stress conditions from α-linolenic acid. However, their epimers with relative prostaglandin configuration termed phytoglandins (PhytoG) have never been detected in Nature, likely because of the lack of synthetic reference material. Here, the first asymmetric total synthesis of such compounds, namely of PhytoGF1α (9-epi-16-F1t-PhytoP) and its diastereomer ent-16-epi-PhytoGF1α (ent-9,16-diepi-16-F1t-PhytoP), has been accomplished. The synthetic strategy is based on radical anion oxidative cyclization, copper(I)-mediated alkyl-alkyl coupling and enantioselective reduction reactions. A UHPLC-MS/MS study using the synthesized compounds as standards indicates PhytoG formation at significant levels during autoxidation of α-linolenic acid in edible vegetable oils. Initial testing of synthetic PhytoGs together with F1-PhytoP and 15-F2t-IsoP derivatives for potential interactions with the PGF2α (FP) receptor did…
Rationally Designed Protein-Based Inhibitor of α-Synuclein Fibrillization in Cells
Journal of Medicinal Chemistry 64 (10): 6827–6837 (2021)
Chiral detection by induced surface-enhanced Raman optical activity
Chemical Communications 2021: Early View
Polysubstituted Pyrimidines as Potent Inhibitors of Prostaglandin E2 Production: Increasing Their Aqueous Solubility
ChemMedChem 2021: Early View
Maintenance of organellar protein homeostasis by ER-associated degradation and related mechanisms
Molecular Cell 2021: Early View